7 Biggest Mistakes I’ve Personally Made as a Lifestyle Entrepreneur

By Sean Ogle •  Updated: 06/06/13 •  10 min read

“While one person hesitates because he feels inferior, the other is busy making mistakes and becoming superior.” – Henry C. Link

Earlier this week I shared with you the 7 biggest mistakes I’ve seen beginning lifestyle entrepreneurs make when starting their businesses.  Ever since I posted that I haven’t been able to stop thinking about my own mistakes that I’ve been making.

I’m far from perfect with my business, and there are some mistakes I’ve made that have definitely been haunting me over the last year as I continue to build and scale things over here.

So I guess I figure that if I’m still dwelling on this a couple days later, then you’ll probably get some value out of me getting really open, and just laying it all out there.

So here you go.

These are the 7 biggest mistakes I’m currently making in my business, as well as a little insight into why I’ve made them, and what I’m doing to fix it.

I’m really not necessarily looking for any feedback on this stuff.  I could give you a hundred things I could do for any one of these things, it really comes down to me just making conscious decisions about where I want things to go, and what I’m going to make a priority over the coming months.

1) Not Establishing Relationships with Big Influencers

I’m kind of in this weird middle ground when it comes to entrepreneurship. I have more drive and motivation than many of the people who just want a thousand bucks and a backpack, but I’m not necessarily looking to build a $100 million business either.

There are a few people who I’ve seen really thrive lately by relentlessly pursuing friendships, mentorships, and relationships with people who have had more success than them.

Scott Dinsmore is one who has been particularly impressive.  His site Live Your Legend really hasn’t been around that long, but he’s built friendships with some of the most successful people online, and has truly taken everything they’ve said to heart, and scaled his business quickly.

Dane and Andy of The Foundation have done the same thing, on an even larger, more profitable scale.

Now, I’ve met and know a lot of successful entrepreneurs, but I haven’t gone above and beyond. I haven’t tried to write guest posts on their blogs or worked to create partnerships that have the potential of reaching a much larger audience.

This is a huge missed opportunity, and one of the things I want to change the most over the coming months.

2) Not rounding out my product offerings

This one is a little bit more complicated.  I have three primary products Overcoming the Fear of Uncertainty, Location Rebel Academy, and Hacking the High Life.

Soon they will all be merged into one site, as it truly is the “perfect lifestyle business course”. Overcome your fears to make a major life change, build the online business, live the life you’ve always wanted. It’s awesome and a ton of people have had success with it.

That said, I’ve got a lot of ideas for what’s next but haven’t decided exactly what that’s going to be.  Last year I made the conscious decision to double down on Location Rebel because it has been so successful, and it’s only gotten better.

While no matter what, that will be the core of my business, it’s time to start thinking about what the next big product is, and how it’s going to relate to the existing community.

I’m lucky. I have a big list of subscribers and followers that have proven they will happily buy if I give them a product that truly blows them away with results and value – I could be leveraging that much more than I am, which would help more people, and make me more money in the process.

#3) Poor General Wellness Habits

This is the absolute biggest mistake I’ve made, hands down.

I go in waves when it comes to positive habits and routines.  Lately, I’ve had a schedule that has me traveling quite a bit for short periods at a time – this is a total routine killer for me.

Right now my routine is wake up lateish (7:30-8), drink 2 cups of coffee, work for a few hours, pretend to work for a few mores, and then go out and drink/eat un-healthy food at night.  It’s a good social routine, but terrible overall wellness routine.

I know what I have to do in order to not only perform at my best, but be happy as well. It’s stupid simple: Wake up early, eat healthy, exercise.

Wow, shocker right?

Lately, I’m lucky if I do one of those things on any given day. And it makes such a remarkable difference when I put all of those things together.

When you not only work for yourself, but by yourself, these things carry even more importance.  They can help break up work periods, which makes you more productive. When I’m doing these things I get more done, and thus have more time to do things I like to do (even more important now that the summer weather has shown up here in PDX).

This is applicable for every single person reading this. Are you struggling in your business? Get your shit together when it comes to general wellness, and I promise you it will have a positive impact on your work.

Less time in front of a computer, doesn’t by any means, equate to less output.

4) Too much lifestyle, not enough business

This may be less mistake and more learning process.  In the past I’ve said, when given the opportunity for fun or work, I’ll almost always choose fun. Why? Because that’s one of the primary benefits of this lifestyle.

Lately, however I’ve maybe veered too much towards the lifestyle and not enough the business.

A lot of this falls back on the fact I work by myself and have a terrible case entrepreneur’s ADD.  I have no problem spending 8 hours in front of a computer, the issue is that rarely is even the majority of that time well spent.

So I’ll often “work” for 6 hours and then go out and do fun stuff in the afternoons and evenings.  If I really worked early on, this would be the perfect balance, but I’m not getting enough done during my work times to justify the amount of playing I do when the weather is good.

So is this a mistake? Probably not, I certainly don’t regret any of it.  It’s more a matter of finding ways to be your most productive self, and the real mistake is not devoting more time to figuring out how to be that super productive, focused person thats lying inside of me.

5) Not Optimizing Email/Sales Funnel

My sales funnel for my products are good, but not great.  The biggest problem is that they conflict with each other. If you sign up for both the Location 180 and Location Rebel email lists at similar times, you end up getting more emails from me than you probably should.

This simple fix would do a number on conversions, and while I have a great plan for this that I’m working on, it’s taken much longer to materialize than I initially thought – see mistakes 3 and 4 above.

That said, bear with me, as it is getting closer, and this means a LOT of really useful free material for you.

While I get a lot of compliments on my emails, I’m still not sure I’ve struck the perfect balance between providing truly useful stuff and talking about myself. Sometimes it falls too far to the latter, which I’m not happy with.

The bottom line, is I truly believe email is the most powerful marketing tool we have as lifestyle entrepreneurs.  I generally know what to do, but the implementation hasn’t been as good as it needs to be.

6) Not Failing More

It’s been a little while since I did something that I’d consider an all out failure.  While you never want to fail, when you do, it usually means you’re taking a risk, trying something new, and learning a ton in the process.

I’ve had some projects or services that haven’t gone as well as I’d hoped, but none have been outright failures.  There are some things I’ve thought about doing, but haven’t due to a variety of factors, most of which are based on the fear of failure.

I’ve hammered home the idea that there is only one fear in the world, uncertainty.  In many aspects of my life, I’m able to successfully view it as an asset and take calculated risks.  However, sometimes it’s easier to stay with something that works (to a point), is comfortable, but isn’t necessarily catapulting you forward.

I need more catapulting in my life, even if that does result in the occasional flop.

7) Poor Long Term Planning

Finally we have another one of the really big mistakes: poor long term planning. I’ve been talking about a few BIG initiatives for the last year. Things like a Location Rebel event, full overhaul of all my sites, and more, but because I haven’t committed and haven’t truly put together a long term plan, none of those big projects have gotten very far.

I still write my blog posts the day before (or day of) posting them. There’s no editorial calendar. Much of what I do is just kind of played day to day or week to week, and I use the excuse of “enjoying the lifestyle” to justify that.

That being said, with more organization and planning, I wouldn’t necessarily need to cut out any of the fun.  It’s simply a matter of getting all of the pieces to play together nicely.

Hollis Carter is one of the most impressive examples of this. He’s built a 7 figure business in numerous industries, and you know why he’s done this? It’s simply so he can ski as many days of the year as possible. He’s automated everything, he does the stuff he loves, and has systems in place that allow him to hand off the stuff he doesn’t want to do.

This isn’t possible without a plan.

Why am I Sharing This?

I’ve been pretty open and vulnerable at times on this site, yet for some reason, this post has me more nervous than most similar posts I’ve shared.

I think that’s because these 7 things truly are at the epicenter of what I’m currently struggling with right now. 

Why am I posting it? A few reasons.

First, I know you’ll get some value. Most of the bloggers, authors, and entrepreneurs out there will only go surface deep with their biggest issues. They need to be seen as experts and authority figures, so usually you’ll just see the good stuff.

I don’t think your opinion of me as an expert in my space is going to change because of this, and in fact I think there’s a good chance it will only increase any respect you have for me (you know, assuming there is some haha).

But more importantly, writing this sucks. Admitting you aren’t the best at something isn’t fun. And I don’t want to write another post like this.

So the goal is to put it out there as a reminder to myself to do better. I’m by no means doing poorly, and judging by what my life looks like I think I’ve made better life choices than a lot of people – but I know it could be even better.

That’s what this is about, focusing on the things that are hard and overcoming them in order to take things to a new level.

So take a leap with me, share what your biggest mistake or struggle is in the comments, and together, as a community, we’ll continue to live lives we’ve only dreamed of.

Sean Ogle

Sean Ogle is the Founder of Location Rebel where he has spent the last 12+ years teaching people how to build online businesses that give them the freedom to do more of the things they like to do in life. When he's not in the coffee shops of Portland, or the beaches of Bali, he's probably sneaking into some other high-class establishment where he most certainly doesn't belong.
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41 comments on "7 Biggest Mistakes I’ve Personally Made as a Lifestyle Entrepreneur"

  1. Rae says:

    I think it’s a good reminder for those of us who are pursuing success at your level (and haven’t even raised our eyes to seven-figure folks) that you aren’t perfect and we don’t need to be perfect to get where we want to be, which is basically what you are saying when you say you need to fail more and not be hobbled by uncertainty. For me, “I have no problem spending 8 hours in front of a computer, the issue is that rarely is even the majority of that time well spent” is a big problem I have, too. I got laid off and I’m happy for it: I’m not in the poorhouse yet, and I have all the time in the world to spend on my niche sites. And I easily spend 8-12 hours a day on the computer, because I’m really crushing it! Except…crushing it looks a lot like updating Twitter and Facebook and reading about all the awesome things other people are doing… Keep going, Sean! Your drive is inspiring.

    1. Sean says:

      Thanks Rae, I appreciate your openness! I think you hit on a good point, you absolutely don’t have to be perfect to be successful…SO far from it.

  2. Great post dude. I was actually just beginning to write a post on “mistakes in life” and it got me thinking about this as well. At least you realize it, which is important. Like RAE above, I too have difficulty being at a computer for eight hours. Some days, I make sure I work 10 hours but those 10 hours are not equal in productive But I feel bad if I don’t spend those kind of hours. Something I need to get over.

    Totally get where your coming from and it’s nice to know I’m not alone with some of these things.

  3. Sean,

    Late in 2012 I ran a IndieGogo campaign for my headphone company: HeadCase Sound.

    I studied the electronics and ‘knew’ that I was in the process of creating a product that would revolutionize the industry.

    I was so naive. I thought that people would flock to my ‘brilliance’.

    The campaign made 10k in the first week and I thought I was home free.

    Unfortunately, that was about it. After that first week, we flopped and didn’t make much the rest of the way. I felt like a total goof.

    After a month of wallowing in my misery I realized that my failure presented a unique learning opportunity. I got back on my horse and contacted all the successful campaigns of the previous months to figure out what I did wrong. I learned what it took for them to make it. I found out that many of the most successful crowd funding campaigns of all time happened on their 2nd or 3rd attempt.

    At first it was hard to even show my face to the people that followed along with my journey. I had been so confident and sure of my campaign that I was embarrassed beyond belief.

    Early this year I’ve used that shameful defeat to revamp the project for a 2013 re-release, expanded my manufacturing company more than I could have imagined, and started a blog (www.thefiveyearproject.com) documenting the entrepreneurial journey.

    In the next month I will be releasing a blog post about this failure and how I used the biggest shame of my life to conquer things I didn’t know I had in me. Would love to show it to you for a potential guest post.

    Failure is a necessary part of success.


    1. I appreciate your last line, Josh. I hate to be the guy that says “look at what I just did” in the comments section – BUT I just wrote about that very thing this morning on my site. You might be interested. 🙂

  4. Matt says:

    great post Sean and a good complement to the general list of mistakes in the other post as well. This is even better because it’s more personal and also a diff. take on the bigger things you’re dealing with and a great reminder for us all. Keep it up.


  5. Jessica says:

    This post really resonated with me. When I was still working as an attorney, dreaming of starting my own business, I thought I had the working from home thing all figured out: I’d get up at 5, go to 6am Bikram yoga, be back at my desk by 8-8:30 and follow a strictly regimented schedule of recipe creation, blog posting, social networking and relationship development. Then around 5 I’d “clock out” for the day…read, work on my novel, see friends, etc.

    Needless to say, my days don’t look anything like what I had envisioned. It’s mostly internet surfing and procrastination, then spending my weekends cramming in all the stuff I was supposed to get done during the week. Not exactly the “lifestyle” I had hoped for! This morning, I had coffee with some women who are also solo entrepreneurs and it turns out that all 3 of us have this problem. We decided to send out periodic emails to one another with our goals and deadlines to keep one another accountable. We’ll see how that works out.

  6. Nely says:

    I loved this post Sean! It shows your honesty and I respect that.

    I don’t like to always read the “happy” posts on websites. I know things are not always perfect, and it is a disservice when bloggers only show the good – and not the bad or the ugly. ( Not that we want to read about the bad constantly, but you know what I mean ) 🙂

    So thank you for being more transparent! And now I better get back to work. 🙂

  7. Neil says:

    That took guts! We should all be so inspired to do the same.

  8. Anouk says:

    Hi Sean,

    Respect, that couldn’t have been easy! and, glad to know your human 🙂

    I’m currently trying to solve the ADD-computer-habits by forcing myself to only open my laptop if I know exactly what I’m gonna do. I even write it down. Once I reach that goal/finish the task, I literally close my laptop, figure out my next task and repeat.

    If (or should I say when) I get distracted, I write that down too. Sometimes it’s actually important, so that could then be my next task. Once I’m done for the day, I allow myself some FB and random blog reading time (wouldn’t want to miss posts like these..).

    I haven’t tested this long enough to call it a success, but so far I’m happy with the results!

    1. Mike says:

      Hey There 😉 I knoow it works…I actaly use a 30 min monitoring scheme.My mentor told me to write down evry 30min, for a month and see where all my time is spent.and truly creating micro-goals has made me achieve more than i had ever imagined.
      The greatest things are made by the smallest steps

  9. Anna says:

    Sean, great post! Your open honesty evens the playing ground for those of us who have doubts about what we are doing. I personally felt a sense of relief because I am struggling with a few of those as well (1,2,6) and it helps to know that it’s not unusual.

  10. Don Neubaum says:

    As your Strategic Management Prof, it hurts my heart to hear that you have not done enough long-term planning. 🙂 What would the Early Breakers think? I guess it is a good thing you have come to this realization. Success is largely a function of is good planning and great execution. Your list of mistakes seems to be a reflection of those realities.

    1. Sean says:

      Holy crap, this just made my day. Good to hear from you!

      Maybe one day I’ll get reaaaaally open and post the song 🙂

  11. Jeff says:

    Thanks for another awesome post Sean! I think I have had issues with all of these at one point or another. The biggest mistake I have probably made is being too analytical and not moving forward because of it. Being analytical is both a blessing and a curse but it can impede progress left unchecked. Not everything needs to be perfect, lets keep making progress 🙂

  12. Hermine says:

    Hey Sean,

    I’ve been following your site for quite some time and honestly, I think stuff like this is great to put out there for your audience to see.

    Personally, I like knowing that even experts struggle too, it’s part of being human and part of our journey as entrepreneurs. It’s good to share these types of things. It builds trust and shows that building a real, lasting business really does take hard work and effort and isn’t just about shiny, perfect blog posts that show people how to replicate your success. Entrepreneurship gets downright messy sometimes!

    I appreciate you being so open and honest about what you’ve been struggling with to get your business to the next level because these are also many of the same things I (and I’m sure many others) struggle with as well.

    For me, I think my biggest struggle has been focusing on getting things done and overcoming my fears of putting myself out there (these two really go hand in hand for me). I’ve been getting a lot better at that as of late though, so I think it’s time to kick things into high gear and start setting some measurable goals for myself, finally.

  13. Hey Sean, thank you for always having our best interests in mind.

    Here’s mind: it’s not a mistake, but it’s a struggle. I told you I’ve recently just quit my job. I consider it my biggest accomplishment to date but I can’t be proud of it yet because first, I need to prove that that was the right decision to make. And that’s terrifying.

  14. Peter Santenello says:


    I’m not sure if your purposely trying to do this or not, but… when you show your flaws/humanity, you create more credibility. By creating credibility you make me want to read your blog more. Awesome work!


  15. Dave says:

    Really great post Sean!

    I think seeing some insight into what my mentors struggle with, of which you are one (even if you didn’t know it!) if so great given that it helps remind me what success is and what it takes, while reminding me of the imperfection and struggle it really is.

    I love these type posts because it adds more layers to my ‘Sean’ experience, and makes me feel more like a friend and equal than someone chasing someone else’s success, if that makes sense.

    Keep up the good work, I’m learning a lot:)


  16. Paul says:

    Couldn’t agree more with the point about health and wellness. It truly is one of the primary cornerstones in building a productive and successful business (and life!)

    It’s also refreshing to know you only you’re far from perfect, as many have said above.

    I often expect myself to put in 8-10 hour days, with nearly perfect productivity (I’m probably reading Tynan’s blog too much), and when I come up short, feel quite disappointed.

  17. Hey Sean!
    I appreciate your humility and vulnerability. It makes me want to read and listen to you even more. Sometimes when I read from those I admire and learn from, it seems that they are flawless and have it all together…and that can be intimidating and even discouraging.

    So, thanks for sharing your imperfections with us. It’s nice to know you’re human!

  18. Love the vulnerability in this Sean. I know how many of us can relate – and there’s a lot! Me included :). Thanks for the shout out!

  19. Chas says:

    “Our greatest glory is not in never failing, but in rising up every time we fail.” ~Ralph Waldo Emerson
    My mind is racing with so many different thoughts that this post has generated for me. I will try to put them down in a cohesive manner, but, forgive me, if they seem disjointed. First-off, thank you Sean, for sharing the video- perhaps it is because the topic that is covered has a special interest for me, but, I find the video to be awesome and a great deal of help to me.
    Note to Jessica~ your comment strikes a chord with me~ procrastination has been a killer for me.
    Although this might actually be detrimental to me, as an audience member and subscriber of the Location 180 newsletter, it seems like it would be more focused and dynamic if Location 180 were folded into Location Rebel (I am not a member of Location Rebel, but, it just seems like that is your core focus).
    One last thing in the spirit of sharing and to be reciprocal~ there is a piece written by Ryan Holmes, the CEO of HootSuite written about astronaut Chris Hadfield’s life’s journey to being on the International Space Center titled ‘Why It’s Still Important To Follow Your Heart’ posted on LinkedIn, that is well worth reading, if you are on that site. Thanks for a great post, Sean.

  20. Jen says:

    I’ve been blogging for several years but finally this year decided to get my business going and create another website. My big problem is pushing through the fear and getting beyond the whole failure thing. I’ve been working really hard to get out of my comfort zone and build as many value added relationships as possible. Item number one on your list needs to be on my list as well. Thanks for reminding me.

  21. This post is more awesome than you know! We all see ourselves in some part of it and can take away counsel, caution and hope that we can pull it all together and have everything (biz & life) running smoothly at some point.

    Location independence is sometimes a hindrance as our real “work” time is eroded by the fun things we do. We have great freedom to have fun because we aren’t boxed in a cubicle and feel guilty if we DON’T take advantage of it because being able to buy experiences is a great perk of this lifestyle. I’ve been LI since 2007 and I still don’t have the balance perfect.

    Thanks for reminding me how desperately I need an editorial calendar!

  22. Kevin Cole says:

    Hey Sean,

    I really enjoyed this man. It’s always nice to see entrepreneurs who are open and honest about what they are doing well and what they are NOT doing well. Your honesty helps the rest of us on the rise understand that being a lifestyle entrepreneur isn’t all sunshine and rainbows.

    There’s a lot of heavy lifting. Not just with the actual act of building a business, but maintaining the proper balance and living with some discipline. You’re consciously aware of your own flaws and I’m sure you’ll nip each one with time.

    Thanks for sharing this man.

  23. Chris says:

    Hey Sean, it looks like you are trying to cover everything to be a really successful human being.
    Personally, you got me lost in the first few sentences because I was following all the links you put in this post (makes me thinking whether funneling is a great idea or not). Anyway, I think that become more than average on all the areas of life takes a little more time because your concentration heads out to more than one direction.
    Nevertheless, this is not impossible and when you start creating a momentum you will start seeing great results in all areas, such as: work, eating, exercising, family, relationships, etc.

    It’s a good thing you did a personal assessment of your own mistakes because few people can objectively see themselves and even few can improve themselves. I see you are on a good road. Don’t lose focus and thank you for this post!

    Sincerely, Chris

  24. Sean,

    Great post, incredibly valuable!

    As I have been transitioning into a more traveling lifestyle, I find it harder to keep in great shape and maintain a healthy routine when I come back home. My question to you regarding #3:

    Would it be any value you to subscribe to a site that helped you keep fit, whether it was to maintain your health or to get ripped, while traveling and living the ultimate lifestyle (through motivation, tips and tricks, product recommendations, etc)? If so what would you like to see? Do you use anything already to maintain a good health routine that helps you with your current lifestyle?

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  26. Man, putting yourself out there is the real deal.
    I love it.
    It also will keep you accountable to the actions you want to take (as you already know).

    One of the tough items for me is seeing my ideas through and not saying no to people. Recently I’ve started a lot of things (non-profit, new blog project, hip-hop dance class, new local business, etc.) and they are all exciting.
    But when new opportunities are looking at me I always want to say yes, when what I really need to do is say NOOOO!!

    It also doesn’t help that I have Attention Deficit Dis……. Gotta Go Get this Butterfly!!

  27. Chris says:

    Really liked this article, point number 3 was one that I neglected for years. I was so focused on building my site and my brand that I forgot to take care of myself. Can’t mention the number of days i’d down 6 cups of coffee so i could work 12 hours then go to the clubs. Now i’m slowing down and realizing that taking care of myself should be the number one priority not my business.

  28. Jan Koch says:

    Hi Sean,

    thank you so much for sharing this, I know how hard it can be to admit his own failures.
    To avoid making mistake #1, I’m writing this comment, letting you know that I love your blog and I’ve been following it for quite a while 🙂

    I can find myself in what you’ve mentioned, especially in the unhealthy lifestyle (but I’m trying to change this, thanks for encouraging me! ) and in optimizing my email / sales funnel.
    I’m learning a lot on your blog and since I started my entrepreneurial journey in March, I know that I’ve got lots of room for improvement.

    I’ll definitely comment more now, thanks again for sharing your insights!

    Best regards,

  29. Hey Sean,

    Great post man! I know when a speak for everyone when I say we really appreciate your openness. I myself am relatively new at the location rebel lifestyle, but am very familiar with the mistakes you mentioned. The exception being #3) Poor General Wellness Habits, but that’s because I’m an exercise therapist (specializing in Posture Alignment Therapy) by trade. which keeps me on track health wise.

    And speaking of habits, while my wife and I were traveling throughout Europe the last six months I created a “Healthy Habits” automated e-mail series/course for my friends and family which they’ve told me have helped them make some significant positive changes in their lives, health wise. So if you ever need any help creating some new good healthy habits I would be more than happy to add you to the email list. Just keep in mind that it was a side project made for friends and family, so the production value is not up to par with with my usual work (www.thepostureguy.com). But who knows, maybe someday I could turn it into an online course ;).

    Anyway, thanks for always putting out awesome content and I look forward to seeing what’s next for THE “LOCATION REBEL”. Until then…

    Take care and keep moving,

    Justin Archer aka “The Posture Guy”

  30. Carla says:

    OMG! What a great post. I think I have the exact same problems as you do, and the post just gave me an idea of things I can do to better myself. (I wrote them on the notepad on my phone, hopefully that’ll help!) I definitely need to organize myself and establish a goal and an action plan. Right now I feel I’m in the air and need to take steps to take my website to the next level while increasing my income… Really. Stuck. On. That. Mostly, because of not know, not automating, and enjoying the lifestyle too much. Thanks so much for sharing. Maybe you should write the things you did to better each item on future posts.

  31. Evelyn says:

    Great posts. Long term planning is essential to the success of any business (yes, even lifestyle businesses). Hope you are now creating one? Also remember just because you planned it does not mean it will happen exactly the way you planned. The biggest job of a plan is to reel you back in when you get of course and not to create a “crystal ball” for the future.

  32. Nat says:

    I realise this is an old post but I just found it and after having SUCH an unproductive day, (when I’d fully intended to work for all of it) it just feels good to know others out there, (who are also successful at what they do) aren’t always super productive.

    Oh – and also the battle with waking early/exercise/food etc… while I’m getting better at this and good with the exercise part, some of the other elements often go out of the window.

    Anyway, thanks for the good read 🙂

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